I think about how I would want to use it. I've done a fair bit of admin work in my time and worked on what I thought were systems that had just been designed with no thought on their efficient use.

I rarely make then 'pretty', more functional, but then I am not a professional developer.
I'll give you an example of a web form.
Want to book a flight, the date of departure defaults to today. fair enough, but I select Feb next year. Then I select the return date. What do I get?, you've guessed it, today's date?

Drives me around the bend.
When I worked for Lloyds bank, one of the senior people createda DB for us. The combos were all over the shop. the first entry we needed to record was at the bottom, the second somewhere above, the third, well somewhere.

No thought to the phases we had to record.